Cooler weather is finally here, and with it comes a slew of fall-focused food and drink events. Indulge in pumpkin ravioli during an Italian wine pairing dinner, Cabernet-infused bourbon during a sip-and-shop event, and creepy cocktails during a Halloween bar crawl. Don’t miss a watercolor class paired with wine, or a Halloween cocktail pairing dinner with five spooky courses.

Monday, October 17

Caymus TasteMaker Dinner at Ruth’s Chris
The fine-dining steakhouse chain is hosting a series of wine dinners, and the next one features popular Caymus Vineyards. The four-course event – to be held both Monday and Tuesday evenings – features a main course of filet with rosemary charred wild mushrooms, zucchini pancakes with herb crème fraiche, and twice-baked potatoes with bacon lardons and truffle cheese sauce paired with Caymus Cabernet Sauvignon. Dinner is $130 per person, plus tax and gratuity, and begins at 6:30 pm.

Thursday, October 20

Taste of the Trolley
This tasting event and fundraiser features bites from restaurants located along the M-Line Trolley route, but it takes place at the Fashion Industry Gallery (F.I.G.) downtown. More than a dozen participants include Malai Kitchen, Sixty Vines, Haywire, and Primo’s. The event will benefit the McKinney Avenue Transit Authority and there’ll be silent and live auctions, too. The $125 tickets includes an open bar and valet parking. The event will run from 6-10 pm.

Halloween Cocktail Dinner at Urban Rio
The Plano cantina and grill will host a five-course cocktail pairing dinner featuring courses themed around Halloween. In fact, guests are encouraged to arrive in costume for a contest. There’ll be prizes for the top three contestants. Dinner is $54.90 per person and begins at 6:30 pm.

Nonna Night at Saint Rocco’s New York Italian
It’s time for another one of Saint Rocco’s monthly four-course dinner events. This one features fall flavors, including pumpkin ravioli with sage butter, skillet-crusted porterhouse steak with smashed sweet potatoes, and pumpkin cannoli with pumpkin cream. The dinner is $65 per person, plus tax and gratuity, and comes with wine pairings. Dinner starts at 6:30 pm.

Watercolor & Wine at Ellie’s
The Napa-inspired Hall Arts Hotel restaurant will host a watercolor painting class paired with wine on its terrace. The workshop led by a local artist will teach different techniques based on a themed image. The $50 per-person price include a glass of wine, light bites, all supplies, and valet parking. Class begins at 6:30 pm.

Friday, October 21

Bourbon & Vine On Tour
Dallas-based distillery Oak & Eden will toast the re-release of its Cabernet-infused bourbon, Bourbon & Vine, with a sip-and-shop event. Visit Rye 51 clothier in West Village for complimentary neat pours and craft cocktails while shopping the store' fall collection of menswear. The event will take place Friday and Saturday from 3-6 pm.

Saturday, October 22

Plano Food + Wine Festival
The fifth annual event, presented by H-E-B and Central Market, will take place at Legacy West just days before the long-anticipated H-E-B Plano store opens. Participants can purchase a food pass ($55), which includes tastes from 15 restaurants and the H-E-B and Central Market culinary tents. The wine tasting pass ($45) includes 20 wine-tasting tickets. Or get both for $80. The event will run from 12-6 pm.

Bar Ilegal Dallas
Visit Jaxon Beer Garden for a Guatemalan-themed pop-up called Bar Ilegal featuring Ilegal Mezcal. The pop-up is inspired by Café No Se, the first mezcal bar opened outside of Mexico. In addition to mezcal tastings and cocktails, there’ll be free flash tattoos, DJ music, and live music. The party starts early at 4 pm with the band set to take the stage at 8 pm.

New Artisan Distillery Grand Opening
The home of Roxor Artisan Gin and Roxor Botanical Bourbon will celebrate its official grand opening with an all-day party. It will feature specialty cocktails, live music, and bottles signed by distillery owners available for purchase. Visit from 12-9 pm.

Halloween Bar Crawl at Legacy Hall
Put the boo in “booze” during this Halloween-themed bar crawl through three floors and five bars at Plano’s Legacy Hall. The $65 ticket include five bar crawl exclusive drinks, a souvenir glass, and admission to a concert in the Box Garden for the Guns N Roses Experience. Stick around for an afterparty at the Tonic Bar & Lounge. The fun begins at 8 pm.

Monday, October 24

Terilli’s 37^th Anniversary Party
The longtime Greenville Avenue Italian restaurant will celebrate its birthday with a bash. For a $10 entry fee per person, guests can enjoy complimentary beer, wine, barbecue, and bubbly along with a casino party, costume contest, and dancing to DJ music. The theme is Mad Hatter’s Tea Party, so go dressed as a character from the famed fairy tale. The party starts at 7 pm.